data_2012584 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2002 _journal_volume 58 _journal_page_first o136 _journal_page_last o138 _publ_section_title ; Piperazine-1,4-diium--2,4-dinitrophenolate--water (1/2/2) ; loop_ _publ_author_name 'Usman, Anwar' 'Chantrapromma, Suchada' 'Fun, Hoong-Kun' 'Poh, Bo-Long' 'Karalai, Chatchanok' _chemical_formula_moiety 'C4 H12 N2 2+ , 2C6 H3 N2 O5 - , 2H2 O' _chemical_formula_sum 'C16 H22 N6 O12' _chemical_formula_iupac 'C4 H12 N2 2+ , 2C6 H3 N2 O5 - , 2H2 O' _chemical_formula_weight 490.40 _chemical_melting_point '515K (decompose)' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.1140(6) _cell_length_b 12.9702(6) _cell_length_c 6.5813(3) _cell_angle_alpha 90 _cell_angle_beta 99.6460(10) _cell_angle_gamma 90 _cell_volume 1019.44(8) _cell_formula_units_Z 2 _cell_measurement_temperature 183(2) _exptl_crystal_density_diffrn 1.598 _diffrn_ambient_temperature 183(2) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 .69486(11) .52605(10) .2104(2) .0201(3) Uani d . 1 . . O O2 .65629(11) .72209(11) .3258(3) .0261(4) Uani d . 1 . . O O3 .78449(12) .83264(10) .2887(3) .0274(4) Uani d . 1 . . O O4 1.16477(12) .73032(11) .4446(3) .0293(4) Uani d . 1 . . O O5 1.21241(11) .58732(12) .3116(3) .0322(4) Uani d . 1 . . O N2 .75300(12) .74294(11) .3032(3) .0159(4) Uani d . 1 . . N N3 1.14065(13) .64615(12) .3570(3) .0196(4) Uani d . 1 . . N C3 .79589(15) .55678(14) .2386(3) .0145(4) Uani d . 1 . . C C8 .83223(14) .66063(13) .2916(3) .0135(4) Uani d . 1 . . C C7 .94390(15) .68943(14) .3278(3) .0144(4) Uani d . 1 . . C C6 1.02475(14) .61690(14) .3082(3) .0145(4) Uani d . 1 . . C C5 .99577(15) .51553(14) .2483(3) .0170(4) Uani d . 1 . . C C4 .88576(15) .48688(15) .2156(3) .0175(4) Uani d . 1 . . C H7 .9620(18) .7579(16) .367(3) .020(6) Uiso d . 1 . . H H5 1.057(2) .4637(17) .235(4) .030(6) Uiso d . 1 . . H H4 .8650(18) .4150(16) .176(3) .020(5) Uiso d . 1 . . H N1 .48980(13) .56797(12) .3262(3) .0151(4) Uani d . 1 . . N C2 .48356(15) .60859(14) .5364(3) .0156(4) Uani d . 1 . . C C1 .44851(15) .45924(14) .3032(3) .0161(4) Uani d . 1 . . C H2A .5094(17) .6810(16) .534(3) .018(5) Uiso d . 1 . . H H2B .4035(18) .6062(16) .551(3) .021(5) Uiso d . 1 . . H H2N .4486(19) .6086(16) .219(4) .026(6) Uiso d . 1 . . H H1N .568(2) .5718(19) .299(4) .042(7) Uiso d . 1 . . H H1A .456(2) .4356(17) .171(4) .027(6) Uiso d . 1 . . H H1B .3695(17) .4632(14) .315(3) .013(5) Uiso d . 1 . . H H2W .675(3) .304(3) .020(5) .067(11) Uiso d . 1 . . H H1W .657(2) .400(2) .089(4) .049(8) Uiso d . 1 . . H O1W .62747(12) .34292(12) .0291(2) .0205(3) Uani d . 1 . . O loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 .0133(6) .0191(7) .0293(9) -.0041(5) .0078(6) -.0049(6) O2 .0163(7) .0216(8) .0441(10) .0023(6) .0155(6) .0040(7) O3 .0223(7) .0102(7) .0507(11) -.0002(5) .0085(7) .0006(6) O4 .0183(7) .0238(8) .0452(10) -.0071(6) .0037(6) -.0062(7) O5 .0127(7) .0331(9) .0519(11) .0055(6) .0087(7) -.0037(8) N2 .0142(8) .0142(8) .0201(9) .0015(6) .0052(6) .0010(6) N3 .0140(7) .0198(8) .0255(9) -.0006(6) .0043(6) .0041(7) C3 .0138(8) .0156(9) .0151(9) -.0011(7) .0056(7) .0000(7) C8 .0138(8) .0119(9) .0158(9) .0026(7) .0058(7) .0009(7) C7 .0160(9) .0122(9) .0158(10) -.0003(7) .0048(7) .0015(7) C6 .0102(8) .0162(9) .0180(10) -.0001(7) .0046(7) .0021(7) C5 .0160(9) .0159(9) .0200(10) .0021(7) .0057(7) .0013(8) C4 .0180(9) .0133(9) .0222(11) -.0005(7) .0065(8) -.0035(8) N1 .0126(7) .0129(8) .0208(9) -.0006(6) .0051(6) .0014(7) C2 .0146(9) .0115(9) .0223(10) -.0005(7) .0075(7) -.0020(8) C1 .0133(9) .0135(9) .0219(11) -.0021(7) .0041(7) -.0023(8) O1W .0158(7) .0167(7) .0288(9) .0015(6) .0027(6) -.0037(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C3 . 1.271(2) yes O2 N2 . 1.235(2) yes O3 N2 . 1.2330(19) yes O4 N3 . 1.246(2) yes O5 N3 . 1.230(2) yes N2 C8 . 1.446(2) yes N3 C6 . 1.438(2) yes C3 C4 . 1.444(3) yes C3 C8 . 1.442(2) yes C8 C7 . 1.385(2) ? C4 C5 . 1.365(3) yes C6 C7 . 1.380(2) yes C7 H7 . .94(2) ? C6 C5 . 1.400(3) ? C5 H5 . 1.01(2) ? C4 H4 . .99(2) ? N1 C2 . 1.494(2) ? N1 C1 . 1.496(2) ? N1 H2N . .95(2) ? N1 H1N . .99(3) ? C2 C1 3_666 1.508(3) ? C2 H2A . .99(2) ? C2 H2B . .99(2) ? C1 C2 3_666 1.508(3) ? C1 H1A . .94(2) ? C1 H1B . .98(2) ? O1W H2W . .77(3) ? O1W H1W . .88(3) ?